Josh | Motorcycles, Risk, Freedom, and the Kind of Life You Have to Go Chase
Some people wait until life gives them permission.
Some people buy the motorcycle first.
And every once in a while, somebody decides to stop overthinking it, leave the nest, and find out who they really are out on the open road.
This episode is about freedom.
I sat down with my buddy Josh — aka “I Am Riding Places” — for a conversation about leaving behind a successful chapter, betting on himself, buying a 25-year-old Harley sight unseen in Florida, and riding it solo all the way back to California. Along the way, we got into motorcycles, Americana, fear, risk, purpose, documenting your life, and what happens when you stop asking “what if it goes wrong?” and start asking “what if it goes right?”
Josh spent the better part of a decade riding Harley-Davidsons across the country, documenting small-town America, family legacy, and small business. Then he stepped away from that chapter, gave himself no excuses, and started building something of his own — one mile, one camera roll, and one leap of faith at a time.
This one is about motorcycles.
But it is also about courage.
• 🛣️ Leaving the Nest
Josh talks about stepping away from a great run, knowing when a chapter is over, and taking ownership of what comes next.
• 🏍️ Buying the Bike and Going Anyway
A 25-year-old Harley. Facebook Marketplace. Sight unseen. Florida to California. Solo. Sometimes the best ideas sound a little insane at first.
• 🌎 What the Road Teaches You
From documenting small-town America to meeting people face-to-face, Josh explains what years on a motorcycle taught him about culture, family legacy, and human connection.
• 🔥 Why Risk Matters
No kids. No mortgage. No excuse not to go. This episode gets into the beauty of betting on yourself when life gives you a window to jump.
• 🧠 Underthink It
One of my favorite ideas from this whole conversation: sometimes the way forward is to stop manufacturing fear, quiet the noise, and just go do the thing.
• 🌵 Texas, Wind, Heat, and the Real Ride
Josh shares stories from the road — the wind, the miles, the sunburn, the old-school bike, the screw-down throttle, and the kind of trip that strips life back to basics.
• 📷 Documenting a Life Worth Remembering
Why carrying a camera matters, why the internet can still inspire good things, and why it is worth leaving behind proof that you really lived.
• ⚡ What If It Goes Right?
The whole episode circles around one big idea: fear kills more dreams than failure ever will, and sometimes the only thing left to do is grab the bars and go.
This conversation is about motorcycles.
But deeper than that, it is about becoming.
It is about the version of you at 8 years old.
The version of you at 80.
And whether both of them would be proud of the life you chose to live.
It is about shaking hands.
Making the leap.
Trusting the road.
And realizing the boogeyman is usually a lot smaller than you made him out to be.
This isn’t about playing it safe.
It’s about buying the bike.
Taking the trip.
And coming home changed.
You can find Josh here:
Instagram / YouTube: I Am Riding Places
Creative project: CR8CO.com
And if this one hits you in the chest a little bit, good.
Maybe it means it’s time to go do the thing you’ve been thinking about.